This project is aimed at the development of general synthetic procedures for the preparation of carbohydrates of biological importance. The synthesis of monosaccharides is viewed as a problem in acyclic, stereoselective synthesis whereby two small fragments are joined to afford the carbon skeleton of the target carbohydrate. A new method of glycoside bond formation will also be investigated that involves initial condensation of two fragments through facile esterification of an acyclic carboxylic acid, followed by stereoselective cyclization with reduction. The result of these studies is an extremely flexible approach to carbohydrates that will be applied to the synthesis of medicinally important compounds, including the aminoglycoside antibiotic and a number of therapeutically useful substances combining carbohydrate and non-carbohydrate fragments. With the tools developed in this program it is anticipated that the means will be available for efficient access to compounds otherwise unavailable that may serve as effective drugs and to study, in detail, biological processes implicated in many health problems.